Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2-ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media

被引：76

作者：

Alcaide, B ^{[1
]}

Almendros, P

Rodríguez-Acebes, R

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ, E-28006 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期

关键词：

D O I：

10.1021/jo050130w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of 2,3-indolinediones (isatins) with stabilized organometallic reagents were investigated in aqueous media. Isatins and a variety of stabilized organic halides undergo coupling under Barbier-type conditions in the presence of different metals (indium, tin, zinc) and additives (ammonium chloride, hydrobromic acid, bismuth(III) chloride, hafnium(IV) chloride). The regiochemistry of the processes (carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions) were generally excellent. On this basis, simple and fast protocols for the Synthesis of the potentially bioactive 3-substituted 3-hydroxyoxindole moiety were developed.

引用

页码：3198 / 3204

页数：7

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